I'm interested in this exercise as well. 

Secondly, understanding that cash flow typically plays a significant role in multi-family and commercial property, how does one go about determining if a property's asking price is fair/reasonable?

Make monthly lease payments during the rehab period (that would be applied 100% to the purchase price if option is exercised.

@Russell Fugitt, The QI's telling you to exercise caution in changing title immediately prior to a sale are giving you good advice.  

When the option is exercised, you want to 1031 the proceeds of the sale into another property.You also mention avoiding a big tax bill.As Dave Foster has already said, flip property is not eligible to participate in a 1031 exchange.  

Your financing package also plays a big role in this decision which is the primary quantitative piece of the decision.

But I've never hired for this role before-  so I'd love to get some feedback on my Job Description.What do you think?

I do about one day of work a week in order to cut costs but also for the exercise and experience.

So, the question now is what does the contract allow you to do about it and what will it cost you to exercise said remedies.

I like the way you handled it, realizing that chasing him for back rent would be an exercise in futility.